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Search results; Over 1,000 homes in Radda in Chianti

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Top guest favourite
Villa in Radda in Chianti
Tuscan character, contemporary style and comfort
Business host
26–31 Oct
4.99 out of 5 average rating, 69 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Galendino
Business host
10–17 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Montemarcoli
Individual host
7–12 Nov
5.0 out of 5 average rating, 34 reviews
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Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 15 reviews
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Flat in Radda in Chianti
Cottage
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Villa in Gaiole in Chianti
Villa Ridolfo, a property surrounded by vineyards
Business host
29 Sept – 4 Oct
5.0 out of 5 average rating, 30 reviews
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Top guest favourite
Home in Lecchi
"La Casa di Maria Luce"® with panoramic terrace
Individual host
24–29 Sept
4.96 out of 5 average rating, 245 reviews
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Superhost
Villa in Gaiole in Chianti
Le Granchiaie
Business host
17–24 Oct
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Home in Gaiole in Chianti
Borgo di Gaiole – Stylish Home in Chianti
Individual host
19–24 Oct
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Top guest favourite
Flat in Poggibonsi
Casal De' Matti - Margot House
Business host
26–31 Oct
4.98 out of 5 average rating, 47 reviews
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Guest favourite
Flat in San Gusmè
La Dimora del Luca
Individual host
22–27 Oct
4.98 out of 5 average rating, 171 reviews
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Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
15–20 Oct
5.0 out of 5 average rating, 6 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
7–12 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Villa in Castelnuovo dei Sabbioni
Villa Valdarno Chianti - Private Pool
Business host
26 Jun – 1 Jul
4.92 out of 5 average rating, 36 reviews
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Guest favourite
Villa in Gaiole in Chianti
Corte del Chianti Dependance
Business host
15–20 Apr
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Apartment in Greve in Chianti
Relax in a Chianti Classico winery
Business host
21–26 Sept
4.95 out of 5 average rating, 19 reviews
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Superhost
Apartment in Gaiole in Chianti
Casa Livio, a garden with a view
Business host
10–15 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Monteriggioni
Beautiful Villa with private swimming pool
Individual host
10–17 Oct
5.0 out of 5 average rating, 18 reviews